Asymmetric Synthesis of alpha-Amino Phosphonic Acids by Diastereoselective Addition of Trimethyl Phosphite onto Chiral Oxazolidines(1).

Abstract

A simple and general asymmetric synthesis of alpha-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-alpha-substituted amino phosphonic acids in good overall yields and high ee (77-->97%) after simple deprotection.